"Everyone should get out of their safe zone for a while. The best experiences we have as people are the ones in unfamiliar environments."

Kyle is a freelance reporter at several newsrooms in Asia, including CNN, Quartz and Yahoo. He’s also working toward finishing his bachelor’s degree in communication studies at Nanyang Technological University. In this profile, he talks about the benefits of freelancing as well as the lessons he’s learned along the way.

Kyle appears here as part of our profiles on the evolving generation of professionals in the service of journalism. Follow him on Twitter here.

Photo by Hillary Tan.

You’ve done plenty of freelance reporting work in the past few years. What do you love about freelancing?

I love that I have the flexibility to pick from a wide range of stories for different publishers. Sometimes, being stuck in a certain beat can get quite taxing and tiresome and I relish a change of pace and variety in my work.

Freelancing gives me that freedom to tap on stories from minister comments to drag queens. Also, I can organize my schedule to fit in other duties, such as my full-time communications undergraduate study. Early lunches are a huge bonus 🙂

What’s the best kept secret (until now) about finding freelance jobs?

There’s one big secret and… it’s not really fancy. It’s all about pitching the right story to the right person. Keep listening to important and interesting stories, know which media outlets will probably carry them, then send your pitch through contacts or even file a cold pitch.

Most importantly, have some work out there first, so your credibility is established. While this industry is indeed about who you know, we’re journalists first — it only matters what story we have. Talk to people who want that story.

What would persuade you to take a “regular” corporate job?

A huge support for telecommuting and remote filing would persuade me more. Singapore is far behind other countries when it comes to this and I appreciate the freedom to be able to take care of your other duties especially when they must be done during office hours. Money doesn’t move me so much anymore. Yes, I have to pay the bills, but the support for an “un-corporate” job would be best.

As a reporter, what’s one thing you would like to do better?

I would like to be able to actually do the opposite of journalism: to shut out the noise. It gets too addictive! I’m in Russia now and finding out about the LGBT community here and even then, I’m constantly thinking about story ideas! Sometimes, we all need a break.

What are some of the things you do in this job that would surprise people?

I eavesdrop. A lot. And sometimes, an idea from a discussion with a friend can become a story idea. It’s caused some discomfort at lunch (sorry, friends!) but call it a gut feel, if you will. I sometimes work remote from cafes so that I can listen in on the conversations of others — and once you understand how lives work, news becomes easier because you’re reporting to inform and impact those cafe discussions.

What are your daily habits like? How do you keep up with the pace of news?

I check in at 9am every weekday via my CMS at the Deutsche Press Agency and scan my bookmarks and Google Alerts for emerging stories. Keeping up with the pace of news is quite simple if you’re naturally inquisitive: social media provides good leads and I particularly pay attention to influencers in key sectors in politics and society who may bring up bits of information. Of course, emails form a key part of the daily copy-tasting. I’m lucky to have a pool of contacts that send me leads if they hear of anything — and I’m not afraid to ask if I need to suss out a lead too. It’s an exchange of information, and we are in control of how it turns out.

What is the biggest thing you know today that you didn’t know a year ago?

I didn’t know that freelancing could be a viable career option! It was not a career path I was thinking of a year ago, but the merits of freelancing are very strong. And as long as you’ve gotten the hang of your busy periods and peak workload, it could be an option if you need to fit in other important duties in your calendar. I’ve made some missteps as a freelancer (know your peak periods and don’t overcommit!), but for what it’s worth so far, it’s been great and I’m constantly learning how to make my work fit into my life. It’s an evolving thought.

As a freelancer, how do you create opportunities to keep learning?

I think everyone should get out of their safe zone for a while. The best experiences we have as people are the ones in unfamiliar environments, and when we see how life works over there, we are reminded of the simple values these cultures possess in the quirkiest of ways. It makes news easy to grasp: the values are simple, the ways of life are striking.

Even without courses or new skills to adapt to convergent newsrooms, my best advice would be to grab your passport, go somewhere else and live like the locals do. See how their lives are affected by information and knowledge.

What you do know about motivating young talent in newsrooms that many managers probably don’t get?

Lots of young talent today do not value money and status as much as voice and impact. Newsrooms today seem stuck on HR practices of promotion and “senior” status which may help to afford the finer things in life, but journalists today want their opinions and ideas to be heard and considered.

We do this openly in Popspoken, maintaining communication with writers and placing their voices as part of a biweekly Popspoken Roundtable op-ed column. Ask about what they are listening on the ground and take these story ideas seriously — after all, they are your eyes and ears into the new electorate. Even in reworking newsroom flow, their voice matters.

The Straits Times seems to be doing well in this aspect, getting their younger journalists to report on millennial topics. While there have been comments that it is “off-brand” for ST, a paper that strives to educate the masses should be involving their younger cadre as the voice of their generation.

What kind of a boss would bring out the best in you?

A boss who appreciates my work, leaves me alone when I need to be alone but takes the time to check in and offer tips and advice on angles and moving a story would definitely bring out the best in me.

Surprisingly, bosses who are like friends are a bit difficult to work with because of the line between personal and professional. Friendliness is the best approach. I’ve had a few “tough love” bosses before, and I still respect them because they back it up. To each his own.

What’s the best advice you’ve ever received from a boss?

“Keep it up” — three simple words but they mean a lot when the work behind the stories are recognized. As journalists, information overload and burnout are real and while we can be self-sufficient in the information cycle, getting a nice push is all we need to go forth.

If someone came up to you seeking advice on whether he or she should get into journalism, what would you say?

I’d say this: always keep three stories in your head and relate it closely to your observations on the ground. One of my first few articles with Campus Magazine was an op-ed into LGBT rights in Singapore — a topic that I am very interested in.

The easiest way through the door is not how well you write or how many places you’ve interned at, but what stories and insights you bring to the pitching table. Of course, please come prepared with good grammar and a hand at writing different kinds of stories, but give someone a fruit and they will bite it.

As a media professional, what concerns you most about the future of the industry?

The industry seems to be concerned by “fads”: we have bots feeding information, news apps curating digests. Sadly, it also seems the venture capital scene — one where a lot of news organizations still seem to be reliant on — is focused on these fads instead of the mission of the news organization. Is it relevant? Does it address issues? Does it affect communities?

The cycle of funding here in Singapore is geared towards tech and does not value news as a valuable item anymore. And I think we are missing something here: fads come and go, but news stays. Information is key, communities feed on it and movements spring from them. VCs here need to take a closer look at the true value of credible news in the information cycle and realize that there is a place for them.

If you could choose one problem to solve with tech, what will it be?

Live transcription! It’s the most painful process and while there are a variety of apps out there in the market, having one that most journalists can get behind as an accurate and painless one will greatly help the need to listen to a transcription again.

Also, if I can add another thing to the list, it would be ways to identify online communities and discussions. The market surrounding this is rather vague and still something controlled by social media algorithms, so some development in this aspect will greatly help improve a journalist’s Rolodex.

Leading Millennials

We’re looking for people with an elasticity in their views of media and journalism. It’s rare.

The faces of people in the service of journalism are often found on stage. They are often the heads of their newsrooms. They are often men. There’s little space on stage for the younger people sitting further down the hierarchy of these newsrooms. I want to tell their stories because some of them could one day redefine this industry.